Palladium-catalyzed SN1 reactions of secondary benzylic alcohols: Etherification, amination, and thioetherification

European Journal of Organic Chemistry

Volumn , Issue 7, 2003, Pages 1294-1299

  Miller, Kimberly J ^a   Abu Omar, Mahdi M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Alcohols; Homogeneous catalysis; Nucleophilic substitution; Palladium; Phosphane ligands

Indexed keywords

ANILINE DERIVATIVE; BENZYL ALCOHOL DERIVATIVE; PALLADIUM COMPLEX; SULFIDE;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DIASTEREOISOMER; ENANTIOMER; ETHERIFICATION; THIOETHERIFICATION;

EID: 0037393252     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200390185     Document Type: Article

References (30)

1. J. March, Advanced Organic Chemistry, John Wiley & Sons: New York, 1992, 4th ed, pp. 386-387.
2. D. Braun, K. G. Keppler, Monasch Chem. 1963, 94, 1250-1261.
3. R. E. Balsells, A. R. Frasca, Tetrahedron 1982, 38, 2525-2538.
4. [4a] V. J. Traynelis, W. L. Hergenrother, H. T. Hanson, J. A. Valicenti, J. Org. Chem. 1964, 29, 123-129.
5. [4b] J. Emert, M. Golenberg, G. L. Chiu, A. Valeri, J. Org. Chem. 1977, 42, 2012-2013.
6. [5a] B. Boyer, E. M. Keramane, J. P. Roque, A. A. Pavia, Tetrahedron Lett. 2000, 41, 2891-2894.
7. [5b] E. M. Keramane, B. Boyer, J. P. Roque, Tetrahedron 2001, 57, 1917-1921.
8. [6a] Z. Zhu, J. H. Espenson, J. Org. Chem. 1996, 61, 324-328.
9. [6b] S. AitMohand, S. Lunak, J. Muzart, Chem. Ber/Recl. 1997, 130, 1655-1658.
10. [6c] P. Salehi, N. Iranpoor, F. K. Behbahani, Tetrahedron 1998, 54, 943-948.
11. [6d] G. V. M. Sharma, A. K. Mahalingam, J. Org. Chem. 1999, 64, 8943-8944.
12. [6e] S. Bouquillon, F. Hénin, J. Muzart, Organometallics 2000, 19, 1434-1437.
13. [6f] G. V. M. Sharma, T. Rajendra-Prasad, A. K. Mahalingam, Tetrahedron Lett. 2001, 42, 759-761.
14. [6g] A. Kawada, K. Yasuda, A. Hitoshi, T. Harayama, Chem. Pharm. Bull. 2002, 50, 380-383.
15. 4, see: K. J. Miller, T. T. Kitagawa, M. M. Abu-Omar, Organometallics 2001, 20, 4403-4412.
16. G. D. Yadav, V. V. Bokade, Appl. Catal. A: General 1996, 147, 299-323.
17. A. Baiker, W. Richarz, Tetrahedron Lett. 1977, 18, 1937-1940.
18. F. A. Cotton, G. Wilkinson, C. A. Murillo, M. Bochmann, Advanced Inorganic Chemistry, John Wiley & Sons, Inc: New York, 1999, pp. 1063-1064.
19. P. C. B. Page, S. S. Klair, M. P. Brown, C. S. Smith, S. J. Maginn, S. Mulley, Tetrahedron 1992, 48, 5933-5940.
20. J. Cheng, T. J. Deming, Macromolecules 1999, 32, 4745-4747.
21. G. Chelucci, S. Medici, A. Saba, Tetrahedron: Asymmetry 1999, 10, 543-550.
22. G. Chelucci, M. G. Sanna, S. Gladiali, Tetrahedron 2000, 56, 2889-2893.
23. M. Sperlle, G. Consiglio, J. Am. Chem. Soc. 1995, 117, 12130-12136.
24. F. C. De Schryver, K. Demeyer, S. Toppet, Macromolecules 1983, 16, 89-94.
25. J. F. Gil, D. J. Ramón, M. Yus, Tetrahedron 1993, 49, 9535-9546.
26. S. Kim, K. N. Chung, S. Yang, J. Org. Chem. 1987, 52, 3917-3919.
27. H. C. Brown, J. T. Kurek, M. Rei, K. L. Thompson, J. Org. Chem. 1984, 49, 2551-2557.
28. N. M. Yoon, J. Choi, J. H. Ahn, J. Org. Chem. 1994, 59, 3490-3493.
29. T. Mukaiyama, T. Masui, T. Izawa, Chem. Lett. 1976, 1177-1180.
30. Y. Kikugawa, Chem. Lett. 1981, 1157-1158.